Trifluoroacetic acid → HCID 86727455, compound
Reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@H:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:28][CH2:27][C:20]4=[N:21][NH:22][C:23](=[O:26])[C@@H:24]([CH3:25])[N:19]4[C:18]=3[CH:29]=2)[CH2:11][CH2:10][N:9]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[CH2:1]([C@@H:8]1[CH2:13][C@H:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:28][CH2:27][C:20]4=[N:21][NH:22][C:23](=[O:26])[C@@H:24]([CH3:25])[N:19]4[C:18]=3[CH:29]=2)[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2S,4R)-tert-butyl 2-benzyl-4-((R)-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.190 g, 0.387 mmol) in DCM (3 mL) was added TFA (1 mL) and the mixture was stirred at ambient temperature for 1 h. The solvent was removed in vacuo and EtOAc (2 mL) was added to the residue. The precipitate was collected by filtration and washed with EtOAc (1 mL) and petroleum ether (2 mL) to give (R)-9-((2S,4R)-2-benzylpiperidin-4-yl)-1-methyl-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid (Example #109-2, Enantiomer 2, SFC (Table 1, Method 21) Rt=4.521 min, 0.190 g, 97%) as a solid. LC/MS (Table 1, Method 4) Rt=1.617 min; MS m/z: 391 [M+H]+.
Workup
- customThe solvent was removed in vacuo and EtOAc (2 mL)
- additionwas added to the residue
- filtrationThe precipitate was collected by filtration
- washwashed with EtOAc (1 mL) and petroleum ether (2 mL)
Sources & evidence
- ORD record
- ord-ca731eaf84be4882a802f9fde3d696a8
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115151B2
Reaction notes
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